440 what am I missing here?

Just curious, what ignition did you say your running on it? And what headers again? If your wanting to try a converter, I would recommend calling Precision of new Hampton or PTC, Ultimate, Precision, Pro Torque, etc. and get one custom made. It will help, but I would optimize timing first, just to see. The converter will be a band aid for the cam and cylinder pressure but at least it will let getup into the power band and on the pipe quicker.
Why would trickflow design this topend kit if the lsa was so horrible,and caused compression issues that makes no sense. I will check the timing next time I get the truck out I could be wrong going off of last memory of checking it. As far as headers go I have manifolds on it. Only thing that would fit. Distributor,and coil are E3 parts basically a rebranded blaster type